N-type dopants for efficient solar cells

Patent metadata

Field	Value
Publication number	US-11380852-B2
Application number	US-201916712206-A
Country	US
Kind code	B2
Filing date	Dec 12, 2019
Priority date	Dec 12, 2018
Publication date	Jul 5, 2022
Grant date	Jul 5, 2022

Abstract

Triazabicylodecene can effectively n-dope a variety of organic semiconductors, including PCBM, thus increasing in-plane conductivities. We synthesized a series of TBD-based n-dopants via an N-alkylation reaction and studied the effect of various alkyl chains on the physical and device properties of the dopants. Combining two TBD moieties on a long alky chain gave a solid dopant, 2TBD-C10, with high thermal stability above 250° C. PCBM films doped by 2TBD-C10 were the most tolerant to thermal annealing and reached in-plane conductivities of 6.5×10−2 S/cm. Furthermore, incorporating 2TBD-C10 doped PCBM as the electron transport layer (ETL) in methylammonium lead triiodide (MAPbI3) based photovoltaics led to a 23% increase in performance, from 11.8% to 14.5% PCE.

First claim

What is claimed is:

1. A device, comprising:
an organic transistor, an organic light absorbing device, a solar cell device, a thermoelectric device, a photodetector device, or an organic light emitting device comprising an organic semiconducting region comprising an organic compound comprising an n-type dopant, the organic compound having the structure:

wherein:
0≤m≤8;
0≤n≤8;
1≤x≤4;
R is any substituted or non-substituted alkyl, alkenyl, alkynyl, aryl or alkoxy group and the

comprises the n-type dopant.

2. The device of claim 1 , wherein the organic compound is bonded to a fullerene, or wherein the R comprises a fullerene, so as to n-type dope the fullerene.

3. The device of claim 1 , wherein the organic compound is bonded to a phenyl-C 61 -butyric acid methyl ester (PCBM), or wherein the R comprises PCBM, so as to n-type dope the PCBM.

4. The device of claim 1 , wherein the organic compound comprises the n-type dopant bonded to a fullerene so as to form the organic compound

5. The device of claim 1 , wherein the R is selected so that the organic compound is miscible with an organic acceptor.

6. The device of claim 5 , further comprising a single phase amorphous composition including the organic compound combined with the organic acceptor, wherein the organic compound n-type dopes the organic acceptor.

7. The device of claim 1 , further comprising an ac e region or electron transporting layer including the organic compound.

8. The device of claim 7 , wherein the organic compound is n-type sett-doped such that the organic compound emits electromagnetic radiation in response to current, transports current in a channel of a transistor, or generates current in response to the electromagnetic radiation.

9. The device of claim 7 , wherein the active region or the electron transporting layer includes an organic acceptor combined with the organic compound so that the organic compound n-type dopes the organic acceptor.

10. The device of claim 1 , wherein the organic compound is non-volatile and stable in air up to a temperature of at least 200 degrees Celsius.

11. The device of claim 1 , wherein the R comprises a linker or an electron acceptor.

12. The device of claim 1 , comprising a solar cell device, a thermoelectric device, a photodetector device, or an organic light emitting device, wherein the organic semiconducting region comprises an organic electron acceptor combined with the n-type dopant.

13. A device, comprising:
an organic transistor, an organic light absorbing device, a solar cell device, a thermoelectric device, a photodetector device, or an organic light emitting device comprising an organic compound comprising an n-type dopant, wherein the organic compound has the structure:

wherein:
1≤m≤8;
1≤n≤8;
2≤x≤4; and
R is any substituted or non-substituted alkyl, alkenyl, alkynyl, an or alkoxy group.

14. The device of claim 13 , wherein R contains one or more heteroatoms.

15. The device of claim 13 , wherein R contains one or more aromatic moieties.

16. The device of claim 13 , wherein:

is any of the following bicyclic structures:

17. The device of claim 13 , wherein the n-type dopant is a dimer (x=2) wherein each end of the R is connected to one of the

18. The device of claim 17 , wherein the organic compound is:

19. The device of claim 13 , wherein the n-type dopant is a trimer (x=3) wherein each end of the R is connected to one of the

20. The device of claim 19 , wherein the organic compound is

21. A device, comprising:
an organic transistor, an organic light absorbing device, a solar cell device, a thermoelectric device, a photodetector device, or an organic light emitting device comprising an organic compound comprising an n-type dopant, wherein:
the organic compound has the structure:

0≤m≤8;
0≤n≤8;
1≤x≤4;
R is any substituted or non-substituted alkyl, alkenyl, alkynyl, aryl or alkoxy group; and the

comprises the n-type dopant,
the n-type dopant is, bonded to an organic electron acceptor via the R, or wherein the comprises an organic electron acceptor, so as to n-type dope the organic electron acceptor.

Assignees

• Univ California
• The Mitsubishi Chemical Corp

Inventors

• Schneider Julia
• Chabinyc Michael L
• Wang Hengbin
• Nakayama Hidenori
• Clark Kyle D
• De Alaniz Javier Read

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K30/30

  comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D487/16 Primary

  Peri-condensed systems · CPC title

• B82Y30/00

  Nanotechnology for materials or surface science, e.g. nanocomposites · CPC title